This application claims priority from United Kingdom patent application Ser. No., 0008443.4, filed Apr. 5, 2000.
1. Field of the Invention
This invention pertains to a method for flavoring an ingestible composition with a flavoring agent in organoleptically purified form, unaccompanied by substances of natural origin present in mango. The flavoring agent may be used in a wide variety of ingestible vehicles such as chewing gum compositions, hard and soft confections, dairy products, beverage products including juice drinks and juice products, green vegetable and chicken products, and the like. The present invention also pertains to an ingestible composition comprising an ingestible vehicle and an organoleptically effective amount of the purified flavoring agent. The present invention also pertains to ethyl 4-(thioacetoxy)butyrate represented by the formula, CH3COS(CH2)3COOCH2CH3.
2. Description of the Background
The Generessence™ flavor research program conducted by Bush Boake Allen focuses on developing flavors by employing in depth understanding of the volatile organic components present in a wide variety of samples, for example fruits and herbs and coupling this information to flavor preference profiling. A number of sampling and analytical techniques are used these include extraction and headspace analyses often including the sampling of growing fruit or flowers. The flavors are primarily formulated from synthetic chemicals and contain only components identified in the sample. There is no limit to the concentration of individual components used apart from organoleptic considerations. A problem with developing flavoring agents for fruity and herbaceous materials is that natural fruit materials do not contain a single flavoring agent, but rather contain a complex mixture of volatile components making identification of characteristic flavors very difficult. The volatiles of each sample are analyzed by gas chromatography and a combined gas chromatograph-mass spectrometer.
U.S. Pat. No. 4,007,287 (Evers et al. '287) discloses 3-furyl sulfides having an S-substituent, R1, selected from the group consisting of aralkyl, alkenyl and alkylthioalkyl and a substituent at the 2 position, R2, and a substituent at the 5 position, R3, each selected from the group consisting of hydrogen and methyl. At least one of R2 and R3 is methyl. Evers et al. '287 discloses flavor adjuvants to be propyl propenyl disulfide, methyl propenyl disulfide, methyl propyl disulfide, propyl propenyl trisulfide, allyl propyl disulfide, allyl methyl disulfide, propyl propane thiosulfonate, hexyl propane thiosulfonate, hexyl propane thiosulfinate, hexyl thiopropionate, n-butyl thiopropionate, n-pentyl thiopropionate, n-pentyl thiobutyrate, n-hexyl thioisovalerate, and n-methyl thio-nheptanoate. The 3-furyl sulfides are said to be useful in modifying or enhancing the taste or aroma organoleptic properties of foodstuffs.
U.S. Pat. No. 4,041,186 (Evers et al. '186) discloses 3-furyl sulfides having an S-substituent, R1, which is methylthiomethyl and a substituent at the 2 position, R2, and a substituent at the 5 position, R3, which is hydrogen. Evers et al. '186 discloses flavor adjuvants to be methyl thiazole alcohol (4-methyl-S-β-hydroxyethyl thiazole), 2-methyl butanethiol, 4-mercapto-2-butanone, 3-mercapto-2-pentanone, 1-mercapto-2-propanone, benzaldehyde, furfural, furfuryl alcohol, 2-mercapto-propionic acid, 2-methyl furan-3-thiol, 2-methyldihydrofuran-3-thiol, 2-methyltetrahydrofuran-3-thiol, 2-ethylfuran-3-thiol, 2-ethyldihydrofuran-3-thiol, 2-ethyltetrahydrofuran-3-thiol, 2-propylfuran-3-thiol, 2-isopropylfuran-3-thiol, 2-isopropyldihydrofuran-3-thiol, 2-isopropyltetrabydrofuran-3-thiol, 2-propyldihydrofuran-3-thiol, 2,5-dimethylfuran3-thiol, 2,5-dimethyldihydrofuran-3-thiol, 2,5-dimethyltetrabydrofuran-3-thiol, 2,5-diethylfuran-3-thiol, 2,5-diethyltetrahydrofuran-3-thiol, 2-ethyl-5-methylfuran-3-thiol, 2-methyl-5-ethylfuran-3-thiol, 2-ethyl-5-methyldihydrofuran-3-thiol, 2-ethyl5-methyltetrabydrofuran-3-thiol, 2,5-dipropylfuran-3-thiol, 2,5-diisopropylfuran-3-thiol, 5-isopropyl-2-methylfuran-3-thiol, 2-butylfuran-3-thiol, 2-ethyl-5propyltetrahydrofuran-3-thiol, bis(2-methyl-3-furyl)sulfide, bis(2-methyl-3-furyl)disulfide, bis(2-ethyl-3-furyl)sulfide, bis(2-ethyl-3-furyl)disulfide, bis(2,5dimethyl-3-furyl)sulfide, bis(2,5-dimethyl-3-furyl)disulfide, bis(2-methyl-3-dihydrofuryl)sulfide, bis(2-methyl-3-tetrahydrofuryl)sulfide, bis(2-methyl-3-tetrahydrofuryl)disulfide, bis(2-methyl-3-dihydrofuryl)disulfide, bis(2,5-diethyl-3-dihydrofuryl)sulfide, bis(2,5-diethyl-3-furyl)sulfide, bis(2-ethyl-5-methyl-3-furyl)disulfide, bis(2,5-diethyl-3-furyl)disulfide, bis(2,5-dipropyl-3-furyl)disulfide, bis(2,5-dipropyl-3-furyl)sulfide, bis(2,5-dibutyl-3-furyl)disulfide, bis(5-ethyl-2methyl-3-dihydrofuryl)disulfide, bis(2-ispropyl-3-furyl)sulfide, bis(2-isopropyl-3-furyl)disulfide, bis(2-isopropyl-3-dihydrofuryl)sulfide, bis(2-isopropyl-3-tetrahydrofuryl)disulfide, alkyl pyrazine, methyl pyrazine, 2-ethyl-3-methyl pyrazine, tetramethyl pyrazine, dipropyl disulfide, methyl benzyl disulfide, alkyl thiophenes, 2-butyl thiophene, 2,3-dimethyl thiophene, 5-methyl furfural, acetyl furan, 2,4-decadienal, guiacol, phenyl acetaldehyde, 8-decalactone, d-limonene, acetoin, amyl acetate, maltol, ethyl butyrate, levulinic acid, piperonal, ethyl acetate, n-octanal, n-pentanal, hexanal, diacetyl, monosodium glutamate, sulfur-containing amino acids, cysteine, hydrolyzed fish protein, tetramethyl pyrazine, propyl propenyl disulfide, methyl propenyl disulfide, methyl propyl disulfide, propyl propenyl trisulfide, allyl propyl disulfide, allyl methyl disulfide, propyl propane thiosulfonate, hexyl propane thiosulfonate, hexyl propane thiosulfinate, hexyl thiopropionate, n-butyl thiopropionate, n-pentyl thiopropionate, n-pentyl thiobutyrate, n-hexyl thioisovalerate, and n-methyl thio-n-heptanoate. The 3-furyl sulfides are said to be useful in modifying or enhancing the taste or aroma organoleptic properties of foodstuffs.
U.S. Pat. No. 4,552,770 (Pittet et al.) discloses 4-(hydrocarbylthio)acetoacetic esters having the structure, R2CH2SCH2COCH2COOR1. R1 is a C2-C6 aliphatic hydrocarbyl and R2 is hydrogen or C1-C2 aliphatic hydrocarbyl. The 4-(hydrocarbylthio)acetoacetic esters are said to be useful for augmenting or enhancing the aroma or taste of foodstuffs and chewing gums.
U.S. Pat. No. 4,643,994 (Block et al.) discloses a method of preparing organic trithio oxide compounds by heating and oxidizing oxides of organic disulfides and further discloses antithrombotic uses of the compounds. Specifically, Block et al. discloses organic trithio oxides having the formula, R1—X—R—X1—R1. R is selected from —CH2CH═CH—, —CH2C(CH3)═CH—, —CH—(CH═CH2)—, and CH2. X is selected from —SO— and —SO2—. X1 is selected from —S—S, —S—SO—, and —S—SO2—. R1 is selected from carboxyalkyl, alkoxy, alkylthio, amino, alkylamino and acyl substituted and unsubstituted lower alkyl, lower alkenyl, lower alkynyl, phenyl and lower alkylphenyl. When R is —CH2CH═CH—, X is —SO— and X1 is —S—S—. R1 is not in both instances —CH2CH═CH2 and the total number of carbon atoms of the R1 group when substituted with carboxyalkyl does not exceed ten and the carboxy of the carboxyalkyl includes the esters or alkali metal salts.
U.S. Pat. No. 5,024,847 (Christenson et al.) discloses oxygen and sulfur containing compounds possessing fruity, floral, or woody odors. Specifically, Christenson et al. discloses compounds represented by the formula, (CH3)2C═CH(CH2)2C(CH2XR)═CHCH3. X is sulfur and R is H, lower alkyl, or an acyl group of 1 to 3 carbons. The compounds are said to be used to fragrance or flavor a variety of consumer products such as tobacco products, foodstuffs, beverages, gums, mouthwashes, toothpastes, cosmetics, pharmaceutical preparations, and medicinal products and also provides a process for the preparation of these compounds.
U.S. Pat. No. 5,234,696 (Van Scoik et al.) discloses dietetic formulations for oral use made of tablets formed from dense granules of mixtures of keto or hydroxyamino acid analogs, coated by protective films, which are dissolved in the gastrointestinal juices. The process for obtaining dense granules includes a coordinated increase in pressure being maintained for a substantial period of time and subsequent tableting and coating by immersion or spraying of the granular material. Specifically, Van Scoik et al. discloses the use of L-ornithine α-ketoisovalerate, L-ornithine α-ketoisocaproate, L-lysine α-keto-β-methylvalerate, L-histidine α-ketoisocaproate, calcium α-hydroxy-gamma-methylthiobutyrate, L-tryptophan, L-tyrosine, and L-threonine.
U.S. Pat. No. 5,628,986 (Sanker et al.) discloses oral compositions such as toothpastes, mouthrinses, liquid dentifrices, lozenges and gums containing a phosphate derivative and a copper source. Specifically, Sanker et al. discloses an oral composition comprising from about 0.001% to about 25% of a phosphate derivative having the structure, R[XPO(X″R″)X′]nR′. R is a flavorant component selected from the group consisting of hexanol, octanol, decanol, geranolol, ethyl maltol, para-hydroxy phenylbutanone, phenyl ethyl alcohol, thymol, eugenol, eucalyptol, methyl salicylate, ethyl vanillin, vanillin, cinnamaldehyde, glycerol, acetal, or linalool. R′ and R″ are selected from the group consisting of R, an adherent component, physiologically relevant mono- and divalent cations, and hydrogen. X, X′, X″ are selected from the group consisting of oxygen, nitrogen, and sulfur. n is an integer from 1 to 3.
While the above disclosure provides some insight into the flavoring components, the above disclosure does not provide satisfactory flavoring agents. The present invention provides a novel flavoring agent without the disadvantages which are characteristic of previously known products. The present invention also provides methods for preparing and using the flavoring agents and the ingestible compositions in which it may be employed. cl SUMMARY OF THE INVENTION
The present invention is directed at a method for flavoring an ingestible composition which comprises admixing an ingestible vehicle with an organoleptically effective amount of ethyl 4-(thioacetoxy)butyrate represented by the formula, CH3COS(CH2)3COOCH2CH3.
The present invention is also directed at an ingestible composition comprising (i) an ingestible vehicle; and (ii) an organoleptically effective amount of ethyl 4-(thioacetoxy)butyrate represented by the formula, CH3COS(CH2)3COOCH2CH3.
The present invention is further directed at ethyl 4-(thioacetoxy)butyrate represented by the formula, CH3COS(CH2)3COOCH2CH3.